Thionyl Chloride → 2-Nitropyridine-4-carbonyl chloride
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][N:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].S(Cl)([Cl:15])=O>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][N:12]=1)[C:7]([Cl:15])=[O:8])([O-:3])=[O:2]Participants
3
Procedure
1.8 g. of 2-nitroisonicotinic acid and 30 ml. of thionyl chloride were refluxed for 3 hours. An excess of thionyl chloride was distilled off to leave 2-nitroisonicotinoyl chloride as an oil. The obtained acid chloride was added to 5 ml. of pyridine at -15° C., and to the resulting solution was added 1.5 g. of m-toluylamide. The mixture was stirred at room temperature for 1 hour and the solvent was evaporated at 40° C under reduced pressure. The residue was then purified by silica gel chromatography and recrystallized from ethyl acetate-n-hexane to yield 250 mg. of the desired crystals.
Workup
- distillationAn excess of thionyl chloride was distilled off
Sources & evidence
- ORD record
- ord-b6b584cd7d59490490d506d944686320
- Source dataset
- uspto-grants-1978_07
- Patent number
- US04098893
Reaction notes
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